9-Tricosene

Z)-9-Tricosene [(Z)-CH3(CH2)7CH=CH(CH2)i2CH3] is the sex pheromone of the female housefly. Synthetic (Z)-9-tricosene is used as bait to lure male flies to traps that contain insecticide. Using acetylene and alcohols of your choice as starting materials, along with any necessary inorganic reagents, show how you could prepare (Z)-9-tricosene. 

Cis and trans isomers differ from one another in their physical and, to a lesser extent, their chemical properties. They may also differ in their physiological behavior. For example, the compound ris-9-tricosene... 

The female produced sex pheromone of Aleochara curtula has been described to consist of a mixture of (Z)-7-henicosene and (Z)-7-tricosene [114]. The same compounds are reported to be used by young males as a kind of camouflage to avoid aggression from older males. Similarly, chemical camouflage by using hydrocarbons plays a role in the relations between the myrme-cophilous staphylinid beetle Zyras cones and the ant Lasius fuliginosus. The host worker ants never attack these beetles which show the same profiles of cuticular hydrocarbons as the ants [115]. 

Pheromone gland extracts of the Australian guava moth, Coscinopty-cha improbana (Lepidoptera Carposinidae), contained four compounds that elicited responses from male moth antennae in GC-EAD analyses. These compounds, identified on the basis of GC-MS, were found to be (Z )-7-tricosene along with three monounsaturated ketones, namely (Z)-7-ocatadecen-ll-one, (Z )-7-nonadecen-l l-one and (Z )-7-tricosen-l l-one they were found in a ratio of 65 23-5 1-5 10 respectively. ... 

In contrast, the sex pheromone of the female housefly is (Z)-9-tricosene, a hydrocarbon apparently formed by an oxidative decarboxylative process from a precursor aldehyde by an enzyme that requires NAD-PH and 02 and is apparently a cytochrome P450.140 Oxidative deformylation by a cytochrome P450 converts aldehydes to alkenes, presumably via a peroxo intermediate.117 Formation of an alkene by decarboxylation has also been proposed,141 but a mechanism is not obvious. 

First, identify the constitution of 9-tricosene. Referring back to Table 2.4 in Section 2.8 of the text, we see that tricosane is the unbranched alkane containing 23 carbon atoms. 9-Tricosene, therefore, contains an unbranched chain of 23 carbons with a double bond between C-9 and C-10. Since the... 

Tricosene Decanal 15-0xohexadecanoic acid Heptadecanoic acid methylester... 

Reed J. R., Vanderwel D., Choi S., Pomonis J. G., Reitz R. C. and Blomquist, G. J. (1994) Unusual mechanism of hydrocarbon formation in the housefly cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and C02. Proc. Natl. Acad. Sci. USA 91, 10000-10004. 

A sex pheromone was first demonstrated in the housefly by Rogoff et al. (1964), identified as (Z)-9-tricosene (muscalure) by Carlson et al. (1971) and shown to attract males in an olfactometer at doses as low as 0.07 pg by Adams and Holt (1987). Cis-9, O-epoxytricosane, (Z)-14-tricosen-10-one (Uebel et al., 1978) and methylalkanes (Uebel et al., 1976) are also components of the sex pheromone (Figure 8.1). Adams and Holt (1987) showed that each component has a different role in male courtship behavior. (Z)-9-Tricosene increases male mating-strike activity toward females. The epoxide and ketone decrease the number of homosexual mating strikes, thus acting as sex-recognition factors. The methyl-branched alkanes act as an arrestant and increase the amount of time a male spends with a treated model. 

Figure 8.2 Biosynthesis of (Z)-9-tricosene, 9,10-epoxytricosane and (Z)-14-tricosen-10-one and its regulation in the housefly, M. domestica. Al = aldehyde, Hyd = Hydrocarbon, x z = number of carbons number of double bonds.

Figure 8.6 Effect of development, surgery and hormone treatments on (Z)-9-tricosene production in male and female houseflies. Radio-GLCs of in vivo incorporation of labeled acetate into the alkenes of A ovarian stage 2,3 females, B stage 4 females, C day-6 control female, D day-6 female which had the CA, CC removed within 6 h of emergence, E day-6 female which was ovariectomized within 6 h of emergence, F day-6 female ovariectomized at emergence and treated with one dose of 5 pg 20-HE, G day-6 female ovariectomized at emergence and treated with three closes of 5 pg 20-HE at 24 h intervals, H control male and I males treated with three doses of 5 pg 20-HE at 24 h intervals.

HE into ovariectomized insects over several days resulted in as much (Z)-9-tricosene produced as in intact control females. Application of JH or JH analogs alone or in combination with ecdysteroids had no effect on pheromone production, confirming that JH does not have a role in regulating housefly pheromone production (Blomquist et al 1992). 

The role of hemolymph in transporting hydrocarbons and hydrocarbon pheromones has only recently become fully appreciated. Older models of hydrocarbon formation showed epidermal-related cells (oenocytes) synthesizing and transporting hydrocarbons directly to the surface of the insect (Hadley, 1984). In the housefly, the role of hemolymph is most clearly seen when (Z)-9-tricosene production is initiated. (Z)-9-Tricosene first accumulates in the hemolymph, and then after a number of hours, is observed on the surface of the insect. Modeling of the process (Mpuru el al., 2001) showed that the delay is surprisingly long, more than 24 h are necessary for transportation from site of synthesis to deposition on the surface of the insect. 

Adams T. S., Nelson D. R. and Blomquist G. J. (1995) Effect of endocrine organs and hormones on (Z)-9-tricosene levels in the internal and external lipids of female house flies, Musca domestica. J. Insect Physiol. 41, 609-615. 

Uebel E. C., Sonnet P. E. and Miller R. W. (1976) House fly sex pheromone enhancement of mating strike activity by combination of (Z)-9-tricosene with branched saturated hydrocarbons. Environ. Entomol. 5, 905-908. 

Figure 9.5 Phylogeny and hydrocarbons of the D. melanogaster subgroup. Although the main double bond position was localized on the 6 position in males of the first studied strain (Cobb et al., 1989), recent studies on several different strains have identified position 5 for the most frequent tricosenes (Alves, Lineham et al., unpublished results).

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